SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

(Amendment No. )

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Filed by the Registrant☒

Filed by a party other than the Registrant☐

Check the appropriate box:

☐Preliminary Proxy Statement

☐Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))

☒Definitive Proxy Statement

☐Definitive Additional Materials

☐Soliciting Material under § 240.14a-12

Payment of Filing Fee (Check all boxes that apply):

☒No fee required

☐Fee paid previously with preliminary materials

☐Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11

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ACCOLADE, INC.

1201 THIRD AVENUE, SUITE 1700

SEATTLE, WA 98101

NOTICE OF ANNUAL MEETING OF STOCKHOLDERS

To Be Held On August 8, 2023

Dear Stockholder:

You are cordially invited to attend the Annual Meeting of Stockholders of ACCOLADE, INC., a Delaware corporation (the “Company”), which will be held as a virtual meeting through a live webcast at www.virtualshareholdermeeting.com/ACCD2023. You will not be able to attend the meeting in person. The meeting will be held for the following purposes:

These items of business are more fully described in the proxy statement accompanying this Notice.

This year’s Annual Meeting will be held virtually through a live webcast. You will be able to attend the Annual Meeting, submit questions and vote during the live webcast by visiting www.virtualshareholdermeeting.com/ACCD2023 and entering the 16-digit Control Number included in your proxy card or in the instructions that you received via email. Please refer to the additional logistical details and recommendations in the accompanying proxy statement. You may log-in beginning at 9:45 a.m. Eastern Time, on Tuesday, August 8, 2023.

The record date for the Annual Meeting is June 23, 2023. Only stockholders of record at the close of business on that date may vote at the meeting or any adjournment thereof.

By Order of the Board of Directors

Richard Eskew

Secretary

Plymouth Meeting, PA

June 27, 2023

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ACCOLADE, INC.

1201 THIRD AVENUE, SUITE 1700

SEATTLE, WA 98101

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PROXY STATEMENT

FOR THE 2023 ANNUAL MEETING OF STOCKHOLDERS

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August 8, 2023

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MEETING AGENDA

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ACCOLADE, INC.

TABLE OF CONTENTS

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LETTER FROM OUR CHIEF EXECUTIVE OFFICER

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Dear Shareholders,

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We aspire to build one of the first, customer obsessed nationwide healthcare delivery systems in the United States. Our mission is rooted in the idea that every person should have the opportunity to live their healthiest life, and that this opportunity should not be hindered by an overly complex and costly healthcare system that intimidates people instead of welcoming them. Our Personalized Healthcare solutions are rooted in three very simple principles that we live by every single day:

First, we must deliver flawless service. Service that delivers:

Second, we give our customers a population health strategy, powered by data, for all of the families they cover, not just the top healthcare spenders. And we have the doctors, behavioral health specialists, nurses, pharmacists and care teams to actually deliver that care – virtually – with extraordinary quality. 

Third, in an industry that hasn’t traditionally collaborated well, we believe in enabling innovation through an open platform we call our Trusted Partner Ecosystem. From diabetes management to physical therapy to a variety of other categories, we offer our customers and members access to the best innovations for their personalized healthcare needs. 

At Accolade, it starts with a relationship and grows into Personalized Healthcare. This advocacy-led approach to a superior healthcare experience delivers net promoter scores over 70 for our members and delights our long term customers who benefit from happy employees and lower healthcare costs. If that sounds compelling, over 800 customers and 12 million members agree. We are fresh off a fiscal year when our customers embraced our vision for the future and our market leadership in a growing category became clear. In 2021 we acquired 2nd.MD and Plushcare, two companies that rounded out our offerings in a way that enabled us to begin to deliver a more valuable, differentiated, and unique service to the market. This year, we are unifying our businesses into One Accolade, embracing our role as healthcare disruptors challenging the status quo by singularly focusing on our customers and members. 

As author Fred Reichheld speaks to clearly in his book “Winning on Purpose”, “customer love” yields excellent business results. Last fiscal year, Accolade: 

These successes defined the past year. The macro-economic environment has produced challenges, but as evidenced by our strong financial results, it has also provided opportunity. As the only publicly-traded personalized healthcare company operating at scale, and with our full range of services and partnerships, Accolade raised the bar on the competitive landscape in terms of what it takes to be successful in our market. Our market opportunity and competitive differentiation provide a foundation for years of growth.

In order to press this advantage further, we took steps this year to improve our operations, streamlining our decision-making and moving the company materially closer to positive Adjusted EBITDA. With these initiatives well underway, we are focused on building the first nationwide, customer-obsessed healthcare delivery company in the United States. In every industry, one company sets themselves apart through their fanatical devotion to the customer experience. They build extraordinary customer loyalty by building a culture entirely devoted to serving their needs above all else. They separate themselves from their competition by delivering that value at scale. That leader has not existed in the healthcare industry, and we are building that company at Accolade.

To my colleagues at Accolade, I offer a heartfelt thank you for all your efforts this past year in advancing our mission and supporting our members. You have helped millions of people live better lives and created a new category that is changing how healthcare works in this country. I am proud to stand with you every day.

And to our shareholders, we remain committed to building a truly great and enduring business at Accolade, and your partnership and counsel remain essential elements to our success.

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QUESTIONS AND ANSWERS ABOUT THESE PROXY MATERIALS AND VOTING

Why am I receiving these materials?

We have sent you these proxy materials because the Board of Directors of Accolade, Inc. (sometimes referred to as the “Company” or “Accolade”) is soliciting your proxy to vote at the 2023 Annual Meeting of Stockholders (or the “Annual Meeting”), including at any adjournments or postponements of the meeting. You are invited to attend the Annual Meeting online to vote on the proposals described in this proxy statement. However, you do not need to attend the meeting to vote your shares. Instead, you may simply complete, sign and return the enclosed proxy card, or follow the instructions below to submit your proxy over the telephone or through the internet.

We intend to mail these proxy materials on or about June 27, 2023 to all stockholders of record entitled to vote at the Annual Meeting.

How do I attend the Annual Meeting?

The Annual Meeting will be held virtually through a live webcast at www.virtualshareholdermeeting.com/ACCD2023. You will not be able to attend the Annual Meeting in person. If you attend the Annual Meeting online, you will be able to vote and submit questions, at www.virtualshareholdermeeting.com/ACCD2023.

You are entitled to attend the Annual Meeting if you were a stockholder as of the close of business on June 23, 2023, the record date, or hold a valid proxy for the meeting. To be admitted to the Annual Meeting, you will need to visit www.virtualshareholdermeeting.com/ACCD2023 and enter the 16-digit Control Number found next to the label “Control Number” on your proxy card or in the email sending you the Proxy Statement. If you are a beneficial stockholder, you should contact the bank, broker or other institution where you hold your account well in advance of the meeting if you have questions about obtaining your control number/proxy to vote.

Whether or not you participate in the Annual Meeting, it is important that you vote your shares.

We encourage you to access the Annual Meeting before it begins. Online check-in will start approximately 15 minutes before the meeting on August 8, 2023.

What if I cannot find my Control Number?

Please note that if you do not have your Control Number and you are a registered stockholder, you will need to visit www.virtualshareholdermeeting.com/ACCD2023 on the day of the Annual Meeting to contact the operators who will be able to provide your Control Number to you.

If you are a beneficial owner (that is, you hold your shares in an account at a bank, broker or other holder of record), you will need to contact that bank, broker or other holder of record to obtain your Control Number prior to the Annual Meeting.

Will a list of record stockholders as of the record date be available?

For the ten days ending the day prior to the Annual Meeting, a list of our record stockholders as of the close of business on the record date will be available for examination by any stockholder of record for a legally valid purpose at our corporate headquarters located at 660 West Germantown Pike, Suite 500, Plymouth Meeting, PA 19462 during regular business hours. To access the list of record stockholders beginning on July 29, 2023 and until the Annual Meeting, stockholders should email IR@accolade.com.

Where can we get technical assistance?

If you encounter any difficulties accessing the virtual meeting during the check-in or meeting time, please call the technical support number that will be posted on the Virtual Shareholder Meeting log in page.

For the Annual Meeting, how do we ask questions of management and the board?

We plan to have a Q&A session at the Annual Meeting and will include as many appropriate stockholder questions as the allotted time permits. Questions may be submitted during the Annual Meeting through www.virtualshareholdermeeting.com/ACCD2023.

Who can vote at the Annual Meeting?

Only stockholders of record at the close of business on June 23, 2023 will be entitled to vote at the Annual Meeting. On the record date, there were 75,631,027 shares of common stock outstanding and entitled to vote.

Stockholder of Record: Shares Registered in Your Name

If on June 23, 2023 your shares were registered directly in your name with the Company’s transfer agent, American Stock Transfer & Trust Company, LLC, then you are a stockholder of record. As a stockholder of record, you may vote online at the meeting or vote by proxy. Whether or not you plan to attend the meeting, we urge you to fill out and return the enclosed proxy card to ensure your vote is counted.

Beneficial Owner: Shares Registered in the Name of a Broker or Bank

If on June 23, 2023 your shares were held, not in your name, but rather in an account at a brokerage firm, bank or other similar organization, then you are the beneficial owner of shares held in “street name” and these proxy materials are being forwarded to you by that organization. The organization holding your account is considered to be the stockholder of record for purposes of voting at the Annual Meeting. As a beneficial owner, you have the right to direct your broker, bank or other agent regarding how to vote the shares in your account. You are also invited to attend the Annual Meeting.

What am I voting on?

There are three matters scheduled for a vote:

What if another matter is properly brought before the meeting?

The Board of Directors knows of no other matters that will be presented for consideration at the Annual Meeting. If any other matters are properly brought before the meeting, it is the intention of the persons named in the accompanying proxy to vote on those matters in accordance with their best judgment.

How do I vote?

You may either vote “For” all the nominees to the Board of Directors or you may “Withhold” your vote for any nominee you specify. For each of the other matters to be voted on, you may vote “For” or “Against” or abstain from voting.

The procedures for voting are fairly simple:

Stockholder of Record: Shares Registered in Your Name

If you are a stockholder of record, you may vote online at the Annual Meeting or vote by proxy using the enclosed proxy card. Whether or not you plan to attend the meeting, we urge you to vote by proxy to ensure your vote is counted. You may still attend the meeting and vote at the meeting even if you have already voted by proxy.

Beneficial Owner: Shares Registered in the Name of Broker or Bank

If you are a beneficial owner of shares registered in the name of your broker, bank or other agent, you should have received a voting instruction form with these proxy materials from that organization rather than from Accolade. To vote prior to the meeting, simply complete and mail the voting instruction form to ensure that your vote is counted. Alternatively, you may vote by telephone or over the internet as instructed by your broker or bank. You may access and vote at the meeting by logging in with your Control Number on your voting instruction form at www.virtualshareholdermeeting.com/ACCD2023. However, since you are not the stockholder of record, you may not vote your shares at the meeting unless you request and obtain a valid proxy from your broker, bank or other agent.

How many votes do I have?

On each matter to be voted upon, you have one vote for each share of common stock you own as of June 23, 2023.

If I am a stockholder of record and I do not vote, or if I return a proxy card or otherwise vote without giving specific voting instructions, what happens?

If you are a stockholder of record and do not vote by completing your proxy card, by telephone, through the internet or online at the Annual Meeting, your shares will not be voted.

If you return a signed and dated proxy card or otherwise vote without marking voting selections, your shares will be voted, as applicable, “For” the election of all four nominees for director, “For” the advisory approval of executive compensation, and “For” the ratification of selection by the Audit Committee of the Board of Directors of KPMG LLP as the independent registered public accounting firm of the Company for its fiscal year ending February 29, 2024. If any other matter is properly presented at the Annual Meeting, your proxyholder (one of the individuals named on your proxy card) will vote your shares using his or her best judgment.

If I am a beneficial owner of shares held in street name and I do not provide my broker or bank with voting instructions, what happens?

If you are a beneficial owner of shares held in street name and you do not instruct your broker, bank or other agent how to vote your shares, your broker, bank or other agent may still be able to vote your shares in its discretion. Brokers and nominees can use their discretion to vote “uninstructed” shares with respect to matters that are considered to be “routine,” but not with respect to “non-routine” matters. Under the rules and interpretations of various national and regional securities exchanges, “non-routine” matters are matters that may substantially affect the rights or privileges of stockholders, such as mergers, stockholder proposals, elections of directors (even if not contested), executive compensation (including any advisory stockholder votes on executive compensation), and certain corporate governance proposals, even if management-supported. Accordingly, your broker or nominee may not vote your shares on Proposal Nos. 1 or 2 without your instructions, but may vote your shares on Proposal No. 3. without your instructions.

If you are a beneficial owner of shares held in street name, and you do not plan to attend the meeting, in order to ensure your shares are voted in the way you would prefer, you must provide voting instructions to your broker, bank or other agent by the deadline provided in the materials you receive from your broker, bank or other agent.

Who is paying for this proxy solicitation?

We will pay for the entire cost of soliciting proxies. In addition to these proxy materials, our directors and employees may also solicit proxies in person, by telephone, or by other means of communication. Directors and employees will not be paid any additional compensation for soliciting proxies. We may also reimburse brokerage firms, banks and other agents for the cost of forwarding proxy materials to beneficial owners.

What does it mean if I receive more than one set of proxy materials?

If you receive more than one set of proxy materials, your shares may be registered in more than one name or in different accounts. Please follow the voting instructions on the proxy cards in the proxy materials to ensure that all of your shares are voted.

Can I change my vote after submitting my proxy?

Stockholder of Record: Shares Registered in Your Name

Yes. You can revoke your proxy at any time before the final vote at the meeting. If you are the record holder of your shares, you may revoke your proxy in any one of the following ways:

Your most current proxy card or internet proxy is the one that is counted.

Beneficial Owner: Shares Registered in the Name of Broker or Bank

If your shares are held by your broker, bank or other agent, you should follow the instructions provided by your broker, bank or other agent.

When are stockholder proposals and director nominations due for next year’s annual meeting?

To be considered for inclusion in next year’s proxy materials, your proposal must be submitted in writing by May 10, 2024 to Accolade’s Corporate Secretary at 660 West Germantown Pike, Suite 500, Plymouth Meeting, PA 19462. If you wish to submit a proposal (including a director nomination) at the 2024 Annual Meeting of Stockholders that is not to be included in next year’s proxy materials, the proposal must be received by our Corporate Secretary not

later than the close of business on May 10, 2024 nor earlier than the close of business on April 10, 2024; provided, further, that if our 2024 Annual Meeting of Stockholders is held before July 9, 2024 or after September 7, 2024, then the proposal must be received no earlier than the close of business on the 120th day prior to such meeting and not later than the close of business on the later of the 90th day prior to such meeting or the 10th day following the day on which public announcement of the date of such meeting is first made. You are also advised to review our bylaws, which contain additional requirements about advance notice of stockholder proposals and director nominations.

In addition, stockholders who intend to solicit proxies in support of director nominees other than the Company’s nominees must also comply with the additional requirements of Rule 14a-19(b).

How are votes counted?

Votes will be counted by the inspector of election appointed for the meeting, who will separately count, for the proposal to elect directors, votes “For,” “Withhold” and broker non-votes; with respect to the advisory approval of executive compensation, votes “For,” “Against,” abstentions and broker non-votes; and, with respect to the proposal to ratify the selection of KPMG LLP as the Company’s independent registered public accounting firm, votes “For,” “Against” and abstentions.

What are “broker non-votes”?

As discussed above, when a beneficial owner of shares held in street name does not give voting instructions to his or her broker, bank or other securities intermediary holding his or her shares as to how to vote on matters deemed to be “non-routine” under various national and regional securities exchange rules, the broker, bank or other such agent cannot vote the shares. These un-voted shares are counted as “broker non-votes.”

As a reminder, if you are a beneficial owner of shares held in street name, in order to ensure your shares are voted in the way you would prefer, you must provide voting instructions to your broker, bank or other agent by the deadline provided in the materials you receive from your broker, bank or other agent.

How many votes are needed to approve each proposal?

The following table summarizes the minimum vote needed to approve each proposal and the effect of abstentions and broker non-votes.

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What is the quorum requirement?

A quorum of stockholders is necessary to hold a valid meeting. A quorum will be present if stockholders holding at least a majority of the outstanding shares entitled to vote are present at the meeting virtually or represented by proxy. On the record date, there were 75,631,027 shares outstanding and entitled to vote. Thus, the holders of 37,815,514 shares must be present virtually or represented by proxy at the meeting to have a quorum.

Your shares will be counted towards the quorum only if you submit a valid proxy (or one is submitted on your behalf by your broker, bank or other nominee) or if you vote online at the meeting. Abstentions and broker non-votes will be counted towards the quorum requirement. If there is no quorum, the holders of a majority of shares present at the meeting or represented by proxy may adjourn the meeting to another date.

How can I find out the results of the voting at the Annual Meeting?

Preliminary voting results will be announced at the Annual Meeting. In addition, final voting results will be published in a current report on Form 8-K that we expect to file within four business days after the Annual Meeting. If final voting results are not available to us in time to file a Form 8-K within four business days after the meeting, we intend to file a Form 8-K to publish preliminary results and, within four business days after the final results are known to us, file an additional Form 8-K to publish the final results.

What proxy materials are available on the internet?

The letter to stockholders, proxy statement, Form 10-K and annual report to stockholders are available at www.accolade.com.

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PROPOSAL 1

ELECTION OF DIRECTORS

Accolade’s Board of Directors is divided into three classes. Vacancies on the Board of Directors may be filled only by persons elected by a majority of the remaining directors. Any increase or decrease in the number of directors will be distributed among the three classes so that, as nearly as possible, each class will consist of one-third of the total number of directors. A director elected by the Board of Directors to fill a vacancy in a class, including vacancies created by an increase in the number of directors, shall serve for the remainder of the full term of that class and until the director’s successor is duly elected and qualified.

The Board of Directors presently has nine members. There are four directors in the class whose term of office expires in 2023. Each of the nominees listed below is currently a director of the Company and was appointed to our Board of Directors prior to our initial public offering. If elected at the Annual Meeting, each of these nominees would serve until the 2026 annual meeting and until his or her successor has been duly elected and qualified, or, if sooner, until the director’s death, resignation or removal. It is the Company’s policy to invite directors and nominees for director to attend the Annual Meeting. Six of the directors attended the 2022 Annual Meeting of Stockholders.

Directors are elected by a plurality of the votes of the holders of shares present virtually or represented by proxy and entitled to vote on the election of directors. Accordingly, the four nominees receiving the highest number of affirmative votes will be elected. Shares represented by executed proxies will be voted, if authority to do so is not withheld, for the election of the four nominees named below. If any nominee becomes unavailable for election as a result of an unexpected occurrence, shares that would have been voted for that nominee will instead be voted for the election of a substitute nominee proposed by the Company. Each person nominated for election has agreed to serve if elected. The Company’s management has no reason to believe that any nominee will be unable to serve.

Nominees

The following is a brief biography of each nominee for director and a discussion of the specific experience, qualifications, attributes or skills of each nominee that led our Nominating and Corporate Governance Committee to recommend that person as a nominee for director, as of the date of this proxy statement.

The Nominating and Corporate Governance Committee seeks to assemble a board that, as a whole, possesses the appropriate balance of professional and industry knowledge, financial expertise and high-level management experience necessary to oversee and direct the Company’s business. To that end, the Nominating and Corporate Governance Committee has identified and evaluated nominees in the broader context of the Board of Directors’ overall composition, with the goal of recruiting members who complement and strengthen the skills of other members and who also exhibit integrity, collegiality, sound business judgment and other qualities that the Nominating and Corporate Governance Committee views as critical to effective functioning of the Board of Directors. To provide a mix of experience and perspective on the Board of Directors, the Nominating and Corporate Governance Committee also takes into account geographic, gender, age, racial and ethnic diversity. The brief biographies below include information, as of the date of this proxy statement, regarding the specific and particular experience, qualifications, attributes or skills of each director or nominee that led the Nominating and Corporate Governance Committee to believe that that nominee should continue to serve on the Board of Directors. However, each of the members of the Nominating and Corporate Governance Committee may have a variety of reasons why he or she believes a particular person would be an appropriate nominee for the Board of Directors, and these views may differ from the views of other members.

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Nominees for Election for a Three-year Term Expiring at the 2026 Annual Meeting

Rajeev Singh has served as our chief executive officer and a member of our Board of Directors since October 2015. In 1993, Mr. Singh co-founded Concur Technologies, Inc., a business travel and expense management company. Mr. Singh served on Concur’s board of directors from April 2008 until January 2015 and was most recently its president and chief operating officer until it was acquired by SAP SE in 2014. Prior to Concur, Mr. Singh held positions at Ford Motor Company and General Motors Corporation. Mr. Singh is on the board of Amperity, a privately held technology company focused on customer data management. From March 2017 to October 2022, he served on the board of Avalara, Inc., a tax compliance software company. Mr. Singh holds a B.S. from Western Michigan University. We believe Mr. Singh is qualified to serve on our Board of Directors due to his extensive knowledge of our company, as well as his significant operational and strategic expertise.

Peter Klein has served as a member of our Board of Directors since September 2019 and has served as our lead independent director since June 2021. From January 2014 to June 2014, Mr. Klein served as chief financial officer of William Morris Endeavor Entertainment, LLC, a global sports and entertainment marketing firm. Mr. Klein spent over 11 years in various finance leadership roles at Microsoft Corporation, including serving as chief financial officer from November 2009 until May 2013. Previously, he held senior finance positions with McCaw Cellular Communications, Orca Bay Capital Corporation, Asta Networks Inc. and Homegrocer.com, Inc. Mr. Klein currently serves on the boards of directors of F5, Inc., a software company, Sarcos Technology and Robotics Corp., and Denali Therapeutics Inc., a biotechnology company. Mr. Klein previously served on the board of directors of Apptio, Inc., a software company. He holds an M.B.A. from the University of Washington and a B.A. from Yale University. Our Board of Directors is aware of the number of public company boards that Mr. Klein is serving on and of the policies of certain institutional investors and proxy advisory firms on the issue of “overboarding.” In the period of time since the fiscal year 2022 annual meeting, we have solicited feedback from shareholders about our board composition. Notwithstanding Mr. Klein’s other roles, our Board of Directors believes he has consistently demonstrated an ability to dedicate sufficient time and focus to his duties as a member of our Board of Directors, including by performing his duties as our lead independent director and chair of the Audit Committee and attending all of our Board of Directors and committee meetings in the last fiscal year. Coupling this commitment with Mr. Klein’s qualifications, including his extensive experience as a senior finance executive and as the chief financial officer of one of the world’s largest software companies, we believe Mr. Klein is qualified to serve on our Board of Directors.

Dawn Lepore has served as a member of our Board of Directors since June 2019 and has served as the Chair of the Nominating and Corporate Governance Committee since February 2020. Ms. Lepore is the former chief executive officer and chairman of the board of drugstore.com, an online retailer of health, beauty and wellness products, which she led from 2004 until its acquisition by Walgreens in 2011. Ms. Lepore repositioned drugstore.com to focus on over-the-counter, beauty and vision products, which led the company to record revenues. Prior to drugstore.com, Ms. Lepore spent more than 21 years at Charles Schwab in a variety of leadership roles, including launching Schwab’s highly successful e-commerce business. In her tenure there, she was vice chairman of technology, chief information officer and held strategic positions in operations, administration, business strategy and worked as an active trader. Ms. Lepore has been recognized professionally by multiple industry groups, including Fortune magazine, which nominated her four times as one of the “50 Most Powerful Women in American Business.” Ms. Lepore has also been recognized by the National Organization for Women at their Aiming High Conference, one of InformationWeek’s “Chiefs of the Year” and Future Banker magazine as one of the “Ten Hottest CIOs.” In addition to Accolade, she serves on the boards of loanDepot (NYSE), RealNetworks and Servco Pacific Inc. Ms. Lepore is a graduate of Smith College. We believe Ms. Lepore is qualified to serve on our Board of Directors due to her extensive operational background experience as an executive and director at diverse online consumer, Internet technology and retail companies.

Patricia Wadors has served as a member of our Board of Directors since February 2020. Ms. Wadors has served as the Chief People Officer of Ultimate Kronos Group (UKG) since April 2022. Ms. Wadors served as Chief People Officer of Procore Technologies from November 2020 to April 2022. From September 2017 to November 2020, Ms. Wadors served as the Chief Talent Officer of ServiceNow, Inc. From March 2015 to September 2017, Ms. Wadors served as CHRO-SVP, Global Talent Organization at LinkedIn, and from February 2013 to March 2015, as VP, Global Talent Organization at LinkedIn. From April 2010 to February 2013, Ms. Wadors served as Senior Vice President of Human Resources at Plantronics, Inc., a designer, manufacturer and distributor of headsets for business and consumer applications. Prior to Plantronics, she served as Senior Vice President of Human Resources at Yahoo! and as Chief

Human Resources Officer at Align Technologies, and she has held senior human resource management positions at Applied Materials, Merck Pharmaceutical, Viacom International, and Calvin Klein Cosmetics. Ms. Wadors holds a B.S. in business management with a concentration in human resources management and a minor in psychology from Ramapo College of New Jersey. We believe Ms. Wadors is qualified to serve on our Board of Directors due to her extensive operational background experience as an executive at diverse online consumer and internet technology companies.

THE BOARD OF DIRECTORS RECOMMENDS

A VOTE IN FAVOR OF EACH NAMED NOMINEE.

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Information About Our Continuing Directors

The following is a brief biography for the remaining members of our Board of Directors and a discussion of their specific experience, qualifications, attributes or skills, as of the date of this proxy statement. There are no family relationships among any of our executive officers or directors.

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Directors Continuing in Office Until the 2024 Annual Meeting

Jeffrey Jordan has served as a member of our Board of Directors since July 2016. Mr. Jordan served as a general partner of Andreessen Horowitz, a venture capital firm, from 2011 through June 2023. From 2007 to 2011, Mr. Jordan served as the president and chief executive officer of OpenTable Inc., an Internet and mobile services company. From 2004 to 2006, he served as president of PayPal Holdings Inc., an Internet-based payment system then owned by internet company eBay Inc., and as senior vice president and general manager of eBay from 1999 to 2004. Mr. Jordan currently serves on the board of directors of Pinterest, Inc., a mobile application company, and Airbnb, Inc., a home sharing company. Mr. Jordan holds an M.B.A. from the Stanford University Graduate School of Business and a B.A. from Amherst College. We believe Mr. Jordan is qualified to sit on our Board of Directors due to his experience as an investor and as an officer of technology companies.

Cindy Kent has served as a member of our Board of Directors since January 2021. Ms. Kent has been working in the healthcare industry for more than 25 years. She is the current chief operating officer at Everly Health and was formerly the executive vice president and president of senior living community operations at Brookdale Senior Living, America’s largest senior living company with over 700 facilities across the U.S. She also currently sits on the Board of Trust at Vanderbilt University. Ms. Kent was named one of Savoy Magazine’s “2020 Most Influential Black Executives in Corporate America.” She previously held executive leadership positions at 3M, Medtronic and Eli Lilly. She is a Henry Crown Fellow of the Aspen Institute and was an independent board director at Best Buy. Ms. Kent holds a Master of Divinity as well as an M.B.A. in marketing from Vanderbilt University. She completed her B.S. in industrial engineering and management sciences at Northwestern University. We believe Ms. Kent is qualified to sit on our Board of Directors due to her experience as an executive in the healthcare industry.

Directors Continuing in Office Until the 2025 Annual Meeting

Elizabeth Nabel, M.D. has served as a member of our Board of Directors since June 2021. Following OPKO Health’s acquisition of ModeX Therapeutics in May 2022, Dr. Nabel currently serves as Medical Adviser (part-time) at OPKO Health. She previously served as the president of Brigham and Women’s Hospital and was the first chief health and medical advisor to the National Football League. In her role as director of the National Institute of Health’s National Heart, Lung and Blood Institute, she became known for her advocacy efforts that resulted in the Heart Truth campaign, which features its signature iconic red dress. Dr. Nabel is an elected member of the National Academy of Medicine of the National Academy of Sciences. She has been named one of the nation’s top leaders in medicine by Modern Healthcare magazine, Becker’s Hospital Review and as one of Boston’s “50 Most Powerful People” by Boston magazine. She also serves on the boards of Medtronic, Moderna, Lyell, the Lasker Foundation, and South Florida PBS. She attended Weill Cornell Medical College and completed her internal medicine and cardiology training at Brigham and Women’s Hospital and Harvard University. Our Board of Directors is aware of the number of public company boards that Dr. Nabel is serving on and of the policies of certain institutional investors and proxy advisory firms on the issue of “overboarding.” In the period of time since the fiscal year 2022 annual meeting, we have solicited feedback

from shareholders about our board composition. Notwithstanding Dr. Nabel’s other roles, our Board of Directors believes she has consistently demonstrated an ability to dedicate sufficient time and focus to her duties as a member of our Board of Directors, including by performing her duties as a member of the Audit Committee and attending all of our Board of Directors and committee meetings in the last fiscal year. Coupling this commitment with Dr. Nabel's qualifications, including her medical training and experience as an executive at various healthcare companies, organizations and agencies, we believe Dr. Nabel is qualified to serve on our Board of Directors.

Jeffrey Brodsky joined our Board of Directors in June 2021. Mr. Brodsky is currently a Senior Advisor at Morgan Stanley. He works with management and the board on critical strategic issues related to executive talent, succession, and diversity and inclusion. He helped lead the firm’s COVID-19 response and brings direct experience in acquisition integration, most recently E*TRADE and Eaton Vance. During more than 35 years at Morgan Stanley, Mr. Brodsky held a variety of leadership roles in human resources, culminating in more than 10 years as the firm’s chief human resources officer. Mr. Brodsky is the Chair of the Board for non-profit organization, Safe Horizon. He serves on the Board of Directors for Vialto, Advisory Boards of Private Medical and he was previously on the Advisory Board for the University of Michigan’s Ross School of Business. He earned a B.S. in accounting from Binghamton University. We believe Mr. Brodsky is qualified to serve on our Board of Directors due to his experience with advising executive management teams.

Michael Hilton has served as a member of our Board of Directors since February 2023. Mr. Hilton previously served as our chief product officer from November 2015 through February 2021 and our chief innovation officer from March 2021 through February 2023. Mr. Hilton co-founded Concur and served in various roles from 1993 to January 2015, most recently serving as chief product officer. Prior to Concur, Mr. Hilton served as director of development at Contact Software International, a customer relationship management software company, which was acquired by Symantec Corporation in 1993. Mr. Hilton holds a B.A. from the University of California, Santa Cruz. We believe Mr. Hilton is qualified to serve on our Board of Directors due to his experience as an executive at Concur and Accolade.

INFORMATION REGARDING THE BOARD OF DIRECTORS AND CORPORATE GOVERNANCE

BOARD INDEPENDENCE

As required under the Nasdaq Stock Market (“Nasdaq”) listing standards, a majority of the members of a listed company’s Board of Directors must qualify as “independent,” as affirmatively determined by the Board of Directors. The Board of Directors consults with the Company’s counsel to ensure that the determinations of the Board of Directors are consistent with relevant securities and other laws and regulations regarding the definition of “independent,” including those set forth in pertinent listing standards of Nasdaq, as in effect from time to time.

Consistent with these considerations, after review of all relevant identified transactions or relationships between each director, or any of his or her family members, and the Company, its senior management and its independent auditors, the Board of Directors has affirmatively determined that with the exception of Messrs. Singh and Hilton, all of the Company’s directors are independent directors within the meaning of the applicable Nasdaq listing standards. In making this determination, the Board of Directors found that none of these directors or nominees for director had a material or other disqualifying relationship with the Company.

BOARD OF DIRECTORS LEADERSHIP STRUCTURE

Our Nominating and Corporate Governance Committee periodically considers the leadership structure of our Board of Directors and makes such recommendations to our Board of Directors as our Nominating and Corporate Governance Committee deems appropriate. Our corporate governance guidelines also provide that, when the positions of chairperson and chief executive officer are held by the same person, the independent members of our Board of Directors may designate a “lead independent director.”

Currently, our Board of Directors believes that it is in the best interests of our company and our stockholders for our chief executive officer, Rajeev Singh, to serve as both the Chief Executive Officer and Chairman of the Board of Directors. As Chairman of the Board of Directors, Mr. Singh has authority, among other things, to call and preside over Board of Directors meetings, including meetings of the independent directors, to set meeting agendas and to determine

materials to be distributed to the Board of Directors. Accordingly, the Chairman of the Board of Directors has substantial ability to shape the work of the Board of Directors.

Because Mr. Singh serves in both roles, our Board of Directors has appointed a lead independent director, Peter Klein. As lead independent director, Mr. Klein provides leadership to the Board of Directors if circumstances arise in which the role of Chief Executive Officer and Chairman of our Board of Directors may be, or may be perceived to be, in conflict, and performs such additional duties as our Board of Directors may otherwise determine and delegate, including (i) presiding at meetings of our Board of Directors at which the Chairman of the Board of Directors is not present, (ii) convening meetings of the independent members of our Board of Directors, and (iii) serving as liaison between our Chairman of the Board of Directors and our independent directors. Our Board of Directors believes that its independence and oversight of management is maintained effectively through this leadership structure, the composition of our Board of Directors, and sound corporate governance policies and practices.

ROLE OF THE BOARD OF DIRECTORS IN RISK OVERSIGHT

One of the key functions of the Board of Directors is informed oversight of the Company’s risk management process. The Board of Directors does not have a standing risk management committee, but rather administers this oversight function directly through the Board of Directors as a whole, as well as through various standing committees of the Board of Directors that address risks inherent in their respective areas of oversight. In particular, our Board is responsible for monitoring and assessing strategic risk exposure, including a determination of the nature and level of risk appropriate for the Company. Our Audit Committee has the responsibility to consider and discuss our major financial risk exposures and the steps our management has taken to monitor and control these exposures, including guidelines and policies to govern the process by which risk assessment and management is undertaken. The Audit Committee also monitors compliance with legal and regulatory requirements, in addition to oversight of the performance of our internal audit function. Audit committee responsibilities also include oversight of cybersecurity risk management, and, to that end, the committee typically meets twice annually with the Chief Information Security Officer (“CISO”) and Chief Compliance Officer (“CCO”), as well as the Company’s CEO and CFO, and receives periodic reports from the CISO and CCO, as well as incidental reports as matters arise. Our Nominating and Corporate Governance Committee monitors the effectiveness of our corporate governance guidelines, including whether they are successful in preventing illegal or improper liability-creating conduct. Our Compensation Committee assesses and monitors whether any of our compensation policies and programs has the potential to encourage excessive risk-taking. Typically, the various committees, along with key senior management, including the Company’s chief financial officer, senior vice president of finance, and the Company’s controller, general counsel and chief compliance officer, and chief information security officer, assist the Board of Directors in fulfilling its oversight responsibilities with respect to risk management through regular readouts during the executive session of the full Board by the committees following quarterly committee meetings, and the biannual meetings with the Audit Committee to cover cybersecurity risk. The Board of Directors as a whole receives periodic reports from the head of risk management, as well as incidental reports as matters may arise. It is the responsibility of the committee chairs to report findings regarding material risk exposures to the Board of Directors as quickly as possible. The Board of Directors has delegated to the lead independent director the responsibility of coordinating between the Board of Directors and management with regard to the determination and implementation of responses to any problematic risk management issues.

MEETINGS OF THE BOARD OF DIRECTORS

The Board of Directors met five times during the last fiscal year. Each member of the Board of Directors attended 75% or more of the aggregate number of meetings of the Board of Directors and of the committees on which he or she served, held during the portion of the last fiscal year for which he or she was a director or committee member.

INFORMATION REGARDING COMMITTEES OF THE BOARD OF DIRECTORS

The Board of Directors has three standing committees: an Audit Committee, a Compensation Committee and a Nominating and Corporate Governance Committee. The following table provides membership and meeting information for the fiscal year ended February 28, 2023 for each of the committees of the Board of Directors:

*Committee Chairperson

**Mr. Neff was Chairperson of the Compensation Committee prior to his resignation in February 2023. Mr. Brodsky was appointed Chairperson of the Compensation Committee in April 2023.

+Lead Independent Director

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Below is a description of each committee of the Board of Directors.

Audit Committee

The Audit Committee of the Board of Directors was established by the Board in accordance with Section 3(a)(58)(A) of the Exchange Act, to oversee the Company’s corporate accounting and financial reporting processes and audits of its financial statements. Our Audit Committee currently consists of Mr. Klein, Ms. Lepore, and Dr. Nabel. The chair of our Audit Committee is Mr. Klein. Our Board of Directors has determined that each member of the Audit Committee is independent under the listing standards of Nasdaq and Rule 10A-3(b)(1) of the Exchange Act. Our Board of Directors has determined that Mr. Klein is an “audit committee financial expert” within the meaning of SEC regulations. Each member of our Audit Committee can read and understand fundamental financial statements in accordance with applicable requirements. In arriving at these determinations, our Board of Directors has examined each Audit Committee member’s scope of experience and the nature of their employment. The Audit Committee met six times during the fiscal year.

The primary purpose of the Audit Committee is to discharge the responsibilities of our Board of Directors with respect to our corporate accounting and financial reporting processes, systems of internal control and financial statement audits, and to oversee our independent registered public accounting firm. Specific responsibilities of our Audit Committee include:

Our Audit Committee operates under a written charter that satisfies the applicable listing standards of Nasdaq, which is available on our website at ir.accolade.com/corporate-governance/governance-overview. The inclusion of our website address here and elsewhere in this proxy statement does not include or incorporate by reference the information on our website into this proxy statement.

Compensation Committee

Our Compensation Committee currently consists of Messrs. Brodsky and Jordan and Ms. Wadors. Mr. Neff, who resigned from the Board and all committees in February 2023, served as a member of our Compensation Committee during a portion of fiscal 2023 until his resignation. Ms. Wadors was appointed to the Compensation Committee in April 2023. The chair of our Compensation Committee is currently Mr. Brodsky. Our Board of Directors has determined that each member of the Compensation Committee is independent under the listing standards of Nasdaq and a “non-employee director” as defined in Rule 16b-3 promulgated under the Exchange Act. The Compensation Committee met six times during the fiscal year.

The primary purpose of our Compensation Committee is to discharge the responsibilities of our Board of Directors in overseeing our compensation policies, plans, and programs and to review and determine the compensation to be paid to our executive officers and other senior management, as appropriate. Specific responsibilities of our Compensation Committee include:

Our Compensation Committee operates under a written charter that satisfies the applicable listing standards of Nasdaq, which is available on our website at ir.accolade.com/corporate-governance/governance-overview.

THE SPECIFIC DETERMINATIONS OF THE COMPENSATION COMMITTEE WITH RESPECT TO EXECUTIVE COMPENSATION FOR THE FISCAL YEAR ENDED FEBRUARY 28, 2023 ARE DESCRIBED IN GREATER DETAIL IN THE COMPENSATION DISCUSSION AND ANALYSIS SECTION OF THIS PROXY STATEMENT.

Compensation Committee Interlocks and Insider Participation

None of the members of the Compensation Committee is currently or has been at any time one of our officers or employees. None of our executive officers currently serves, or has served during the last year, as a member of the Board of Directors or Compensation Committee of any entity that has one or more executive officers serving as a member of our Board of Directors or Compensation Committee.

Nominating and Corporate Governance Committee

Our Nominating and Corporate Governance Committee currently consists of Mses. Kent, Lepore and Wadors. The chair of our Nominating and Corporate Governance Committee is Ms. Lepore. Our Board of Directors has determined that each member of the Nominating and Corporate Governance Committee is independent under the listing standards of Nasdaq. The Nominating and Corporate Governance Committee met four times during the fiscal year.

Specific responsibilities of our Nominating and Corporate Governance Committee include:

Our Nominating and Corporate Governance committee operates under a written charter that satisfies the applicable listing standards of Nasdaq, which is available on our website at ir.accolade.com/corporate-governance/governance-overview.

STOCKHOLDER COMMUNICATIONS WITH THE BOARD OF DIRECTORS

Historically, the Company has not provided a formal process related to stockholder communications with the Board of Directors. Nevertheless, every effort has been made to ensure that the views of stockholders are heard by the Board of Directors or individual directors, as applicable, and that appropriate responses are provided to stockholders in a timely manner. The Company believes its responsiveness to stockholder communications to the Board of Directors has been excellent.

CODE OF BUSINESS CONDUCT AND ETHICS

We have adopted a code of business conduct and ethics that applies to our directors, officers, and employees, including our principal executive officer, principal financial officer, principal accounting officer or controller, or persons performing similar functions. Our code of business conduct and ethics is available under the Investor Relations section of our website at ir.accolade.com/corporate-governance/governance-overview. In addition, we post on our website all

disclosures that are required by law or the listing standards of Nasdaq concerning any amendments to, or waivers from, any provision of the code.

CORPORATE GOVERNANCE GUIDELINES

The Board of Directors documented the governance practices followed by the Company by adopting and amending Corporate Governance Guidelines to assure that the Board of Directors will have the necessary authority and practices in place to review and evaluate the Company’s business operations as needed and to make decisions that are independent of the Company’s management. The guidelines are also intended to align the interests of directors and management with those of the Company’s stockholders. The Corporate Governance Guidelines set forth the practices the Board of Directors intends to follow with respect to board composition and selection including diversity, board meetings and involvement of senior management, Chief Executive Officer performance evaluation and succession planning and board committees and compensation. The Corporate Governance Guidelines, as well as the charters for each committee of the Board, may be viewed at ir.accolade.com/corporate-governance/governance-overview.

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BOARD DIVERSITY MATRIX

The Board Diversity Matrix, below, provides diversity statistics for our Board of Directors.

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DIRECTOR COMPENSATION

Non-Employee Director Compensation Policy

Our Board of Directors has adopted a non-employee director compensation policy, pursuant to which our non-employee directors are eligible to receive compensation for service on our Board of Directors and committees of our Board of Directors.

Equity Compensation

Initial Grant

Each new non-employee director who joins our Board of Directors will automatically receive a restricted stock unit award for common stock having a value of $130,200 based on the fair market value of the underlying common stock on the date of grant under our 2020 Equity Incentive Plan (“2020 Plan”), with the $130,200 being prorated based on the number of months from the date of appointment until the date of our next annual meeting of our stockholders. Each initial grant will vest on the earlier of (i) the date of the following annual meeting of our stockholders (or the date immediately prior to the next annual meeting of our stockholders if the non-employee director’s service as a director ends at such meeting due to the director’s failure to be re-elected or the director not standing for re-election) or (ii) the one year anniversary measured from the date of grant, each subject to continued service as a director through the applicable vesting date.

Annual Grant

On the date of each annual meeting of our stockholders, each continuing non-employee director will automatically receive a restricted stock unit award for common stock having a value of $130,200 based on the fair market value of the underlying common stock on the date of grant under our 2020 Plan. Each annual grant will vest on the earlier of (i) the date of the following annual meeting of our stockholders (or the date immediately prior to the next annual meeting of our stockholders if the non-employee director’s service as a director ends at such meeting due to the director’s failure to be re-elected or the director not standing for re-election) or (ii) the one year anniversary measured from the date of grant, each subject to continued service as a director through the applicable vesting date.

Vesting Acceleration

In the event of a change in control (as defined in our 2020 Plan), any unvested portion of an equity award granted under the policy will fully vest immediately prior to the closing of such change of control, subject to the non-employee director’s continuous service with us on the effective date of the change of control.

The calculation of the number of restricted stock units granted under the non-employee director compensation policy will be the closing price of our common stock as reported by Nasdaq on the date of grant.

Cash Compensation

Each non-employee director will receive an annual cash retainer of $86,800 for serving on our Board of Directors and the lead independent director of our Board of Directors will receive an additional annual cash retainer of $25,000.

On an annual basis, a director may elect to receive some or all of the annual cash retainer in the form of additional restricted stock units with an equivalent dollar value at issuance (see “Annual Election” below for more details).

Rajeev Singh, our Chief Executive Officer, is also a director but does not receive any additional compensation for his service as a director. Michael Hilton was formerly our Chief Innovation Officer prior to becoming a director in February 2023. In lieu of receiving non-executive director compensation for his Board service, Mr. Hilton will instead continue to vest in the equity awards he was granted during his time as an employee of the Company until December 31, 2024. Mr. Hilton also will continue to receive health benefits (or equivalent COBRA reimbursement) from the Company until December 31, 2024. Mr. Hilton will not be eligible to receive any non-employee director compensation in any form until after December 31, 2024, at which time he shall be eligible to receive non-employee director compensation consistent with other non-executive directors. See the section titled “Executive Compensation” for more information regarding the compensation earned by Messrs. Singh and Hilton.

The chairperson and members of the three committees of our Board of Directors are entitled to the following additional annual cash retainers:

All annual cash compensation amounts will be payable in equal quarterly installments in arrears, on the last day of each fiscal quarter for which the service occurred, pro-rated based on the days served in the applicable fiscal quarter.

Annual Election

The Board of Directors has approved a director election program, where each non-employee director is allowed to make one or more irrevocable elections with respect to the applicable form and timing of payment of certain compensation payable to such director. The directors are permitted to elect to receive payment of 0%, 50% or 100% of such director’s cash compensation (applicable only for regular annual board service retainer fees and excluding any fees

for being a chair, serving on a committee or amounts paid for service to the Company in any other capacity) for services as a member of the Board of Directors in the form of restricted stock units that vest quarterly over the fiscal year.

If a director elects to receive restricted stock units instead of cash compensation, the director may also elect to defer issuance of the shares of Company common stock issuable upon settlement of the restricted stock unit to a future taxable year following their vesting date. The director may also elect to defer issuance of shares of Company common stock issuable upon settlement with respect to the regular annual grant of restricted stock units made to each director on the date of the Company’s annual meeting of stockholders to future taxable year(s) following their vesting date.

Director Compensation for the Fiscal Year Ended February 28, 2023

The following table shows for the fiscal year ended February 28, 2023 certain information with respect to the compensation of all non-employee directors of the Company:

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PROPOSAL 2

ADVISORY VOTE ON EXECUTIVE COMPENSATION

Under the Dodd-Frank Wall Street Reform and Consumer Protection Act (the “Dodd-Frank Act”), and Section 14A of the Exchange Act, the Company’s stockholders are entitled to vote to approve, on an advisory basis, the compensation of the Company’s named executive officers as disclosed in this proxy statement in accordance with SEC rules.

This vote is not intended to address any specific item of compensation, but rather the overall compensation of the Company’s named executive officers and the philosophy, policies and practices described in this proxy statement. The compensation of the Company’s named executive officers subject to the vote is disclosed in the Compensation Discussion and Analysis, the compensation tables, and the related narrative disclosure contained in this proxy statement. As discussed in those disclosures, the Company believes that its compensation policies and decisions are focused on pay-for-performance principles and strongly aligned with our stockholders’ interests and consistent with current market practices. Compensation of the Company’s named executive officers is designed to enable the Company to attract and retain talented and experienced executives to lead the Company successfully in a competitive environment.

Accordingly, the Board is asking the stockholders to indicate their support for the compensation of the Company’s named executive officers as described in this proxy statement by casting a non-binding advisory vote “FOR” the following resolution:

“RESOLVED, that the compensation paid to the Company’s named executive officers, as disclosed pursuant to Item 402 of Regulation S-K, including the Compensation Discussion and Analysis, compensation tables and narrative discussion is hereby APPROVED.”

Because the vote is advisory, it is not binding on the Board of Directors or the Company. Nevertheless, the views expressed by the stockholders, whether through this vote or otherwise, are important to management and the Board and, accordingly, the Board and the Compensation Committee intend to consider the results of this vote in making determinations in the future regarding executive compensation arrangements.

Advisory approval of this proposal requires the vote of the holders of a majority of the shares present virtually or represented by proxy and entitled to vote on the matter at the Annual Meeting.

THE BOARD OF DIRECTORS RECOMMENDS
A VOTE IN FAVOR OF PROPOSAL 2.

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EXECUTIVE OFFICERS

The following table sets forth certain information with respect to our executive officers as of the date of our Annual Meeting. Biographical information with regard to Mr. Singh is presented under “Proposal No. 1 — Election of Directors” in this proxy statement.

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EXECUTIVE COMPENSATION

COMPENSATION DISCUSSION AND ANALYSIS

This Compensation Discussion and Analysis (“CD&A”) discusses our executive compensation philosophy, objectives and programs, the compensation decisions made under those programs, and the factors considered by the Compensation Committee of our Board of Directors (our “compensation committee”) in making those decisions. The CD&A focuses on the compensation for our fiscal year ended February 28, 2023 (“fiscal year 2023” or “fiscal 2023”), of those individuals who served as our principal executive officer, our principal financial officer and our two other executive officers during fiscal 2023, collectively referred to as our “named executive officers”:

Because we only had four “executive officers” as defined in Exchange Act Rule 3b-7 during fiscal year 2023, we only have four named executive officers (“NEOs”). Richard Eskew, our executive vice president and general counsel, was appointed an “executive officer” as defined in Exchange Act Rule 3b-7 subsequent to February 28, 2023.

Executive Summary

Fiscal Year 2023 Highlights

¹ Adjusted EBITDA is a non-GAAP financial measure that we define as net income (loss) adjusted to exclude interest expense (income), net, income tax expense (benefit), depreciation and amortization, stock-based compensation, acquisition and integration-related costs, goodwill impairment, change in fair value of contingent consideration, severance costs, and other expense (income). See the “Certain Non-GAAP Financial Measures” section of our Annual Report on Form 10-K filed on April 28, 2023 for a reconciliation of these non-GAAP measures to the most directly comparable GAAP measures.

Fiscal 2023 Target Compensation Mix

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Say-on-Pay Responsiveness

At our 2022 annual meeting, we held our first advisory vote on executive compensation which received approximately 47% of the votes cast in support. Following the 2022 annual meeting, the Company held discussions with stockholders representing more than 50% of the shares outstanding to solicit feedback about our executive compensation structure. In those discussions, which were generally part of the Company’s ongoing and regular investor outreach, management heard consistent feedback regarding several issues, including: a preference to see stock compensation more closely tied to performance-related vesting instead of time-related vesting, the implementation of a clawback policy, and a regular review of best practices against industry peers to ensure stronger compensation governance. In response, the Company made adjustments to our executive compensation program. The changes made more closely align executive compensation with the Company’s business performance and achievement of financial objectives as well as to embrace generally accepted best governance practices. For fiscal 2024, our Board of Directors approved the following changes:

The change in the expected mix of long-term incentive (LTI) awards granted to our named executive officers from fiscal 2023 to fiscal 2024 showing this enhanced compensation structure is as follows:

In addition, as part of our fiscal 2023 Proxy process, in advance of the 2023 Annual Meeting, we will be seeking further feedback from stockholders on additional changes that we may make to increase support for our executive compensation in future fiscal years. Our objective is to fairly compensate our executives and attract and retain the best available talent, while also ensuring our executives are aligned to the interests of our stockholders. We believe that such objectives will improve our year-over-year performance on the annual say-on-pay vote. We remain open to and will continue to receive feedback from our stockholders related to our executive compensation program.

Executive Compensation Policies and Practices

We endeavor to maintain executive compensation policies and practices that align with sound governance standards. In fiscal 2024, we are increasing our focus on further aligning executive compensation with performance and adopting and implementing additional policies to better orient the interests of our executives with the interests of our stockholders. Listed below are highlights of our executive compensation policies and practices.

Overview of Compensation Program

Our compensation committee is responsible for establishing, implementing and continually monitoring adherence with our compensation philosophy and executive compensation programs. Our compensation committee strives to ensure that the total compensation paid to our executive officers is fair, reasonable and competitive. Generally, the types of compensation and benefits provided to our executive officers, including the named executive officers, are similar to those provided to executive officers at comparable companies in similarly situated positions.

Compensation Philosophy and Objectives

Our compensation committee believes that the most effective executive compensation program is one that is designed to reward the achievement of our specific annual, long-term and strategic goals, and which aligns executives’ interests with those of our stockholders by rewarding performance above established goals, with the ultimate objective of improving stockholder value. Our compensation committee evaluates both performance and compensation to ensure that we maintain our ability to attract and retain qualified, superior employees in key executive positions and that compensation provided to such executive employees remains competitive relative to the compensation paid to similarly situated executives at comparable companies. To that end, our compensation committee believes that the executive compensation packages provided by us to our named executive officers should include both cash and equity-based compensation that rewards performance as measured against established goals.

Setting Executive Compensation

Role of the Compensation Committee and Executive Officers in Compensation Decisions

The compensation committee is responsible for reviewing and approving the compensation of our executive officers. In this capacity, and based on the foregoing objectives, our compensation committee has structured our executive compensation programs to motivate our executives to achieve the corporate performance goals set by our compensation committee and to reward the executives for achieving these goals. In evaluating executive compensation, our compensation committee considers a variety of factors, including market demands, internal equity and external peer company research and surveys, which provide insight into and guidance on the pay practices of similar companies.

While survey data provides us with helpful guidelines, we do not make compensation decisions based on any single factor.

Our Chief Executive Officer annually reviews the performance of all other executive officers (other than the Chief Executive Officer, whose performance is reviewed by our compensation committee). The conclusions reached and recommendations made based on these reviews, including with respect to salary adjustments and annual incentive award opportunity and actual payout amounts, are presented to our compensation committee, which has the discretion to modify any recommended adjustments or awards to executives.

Our compensation committee has final approval over all compensation decisions for our named executive officers and approves recommendations regarding cash and equity awards to each of our executive officers. Our compensation committee has sole authority over compensation decisions relating to our Chief Executive Officer.

Role of the Independent Compensation Consultant

To assist with the analysis of executive compensation for fiscal year 2023, our compensation committee engaged FW Cook as its independent compensation consultant. FW Cook reports directly to the compensation committee, and the compensation committee has the sole authority to hire, fire and direct the work of FW Cook. For fiscal year 2023, FW Cook advised our compensation committee on a variety of compensation-related issues, including: (1) evaluating the current executive compensation program design to assess its competitiveness and to assist in structuring an executive compensation program that meets the objectives described above; (2) identifying the appropriate mix of compensation components, including base salary, annual incentives and long-term incentives to ensure proper incentive alignment; (3) reviewing the compensation practices of other healthcare technology companies in order to evaluate market trends and compare our executive compensation program with our competitors; and (4) assisting with the development and review of a peer group of companies for formal compensation benchmarking purposes.

Through review and consultation with FW Cook, our compensation committee assessed the independence of FW Cook in light of, among other factors, the independence factors established by Nasdaq. As a result of this assessment, the compensation committee has determined that FW Cook’s work raised no conflict of interest currently or during fiscal year 2023.

Peer Group Development Process and How We Used the Data

Our compensation committee’s decision-making is informed, in part, by reference to a compensation peer group. Our compensation committee reviews and makes adjustments to the composition of the peer group on an annual basis, or more often as deemed necessary, to account for changes in both our business and the businesses of the companies in the peer group. Our compensation committee does not have a specific target compensation level for the named executive officers. Instead, we review data concerning practices at our peer group companies and within the healthcare technology industry as a reference point to assist in developing programs that will attract and retain exceptional talent and drive company performance. The Compensation Committee performs such reviews and analyses as further detailed below.

In April 2022, our compensation committee reviewed our previously-established peer group to be used in connection with making compensation decisions for fiscal year 2023 based on two primary parameters: (1) industry focus; and (2) company size as evaluated primarily based on market capitalization with additional consideration given to revenue. The peer group also factors in companies that are believed to compete with the Company for talent. Specifically, the compensation committee’s selection process focused primarily on healthcare technology companies with similar market capitalizations. This peer group resulted in companies with market capitalization within the range of $800 million (25th percentile) to $3,700 million (75th percentile) with the median being $1,300 million, which at the time of the analysis, closely aligned with the Company’s market capitalization of approximately $1,200 million. Based on these criteria, our compensation committee, in consultation with management, approved a 16-company peer group for fiscal year 2023:

As noted, the Compensation Committee reviews the Company’s peer group annually and, in April 2023, updated the peer group for fiscal 2024 to address certain entities that have been acquired (e.g., 1Life Healthcare, Castlight Health, and Benefitfocus) and/or are no longer appropriate for comparison based on the above-referenced parameters. The updated peer group for fiscal 2024 will be as follows:

Executive Compensation Components

For fiscal year 2023, the principal components of compensation for our named executive officers were: (1) base salary; (2) annual performance-based incentives in the form of a cash bonus and PSUs; and (3) long-term incentive awards pursuant to the 2020 Equity Incentive Plan. As part of fiscal year 2023 compensation, PSUs represented up to 25% of the annual performance-based incentive, and long-term incentive awards comprised a mix of restricted stock units and time-based stock options, which is further detailed below.

Base Salary

We provide our named executive officers and other employees with base salary to compensate them for services rendered during the fiscal year. Base salaries established for our named executive officers are intended to reflect each individual’s responsibilities, experience, historical performance and other discretionary factors deemed relevant by our compensation committee and have generally been set at levels deemed necessary to attract and retain individuals with superior talent. Base salaries are also designed to provide our named executive officers with steady cash flow during the course of the fiscal year that is not contingent on short-term variations in the Company’s operating performance. The initial base salary for our named executive officers is established in their employment agreements or written offer letters, as applicable.

Salary levels are reviewed annually as part of our performance review process as well as upon a promotion or other material change in job responsibility. Merit-based increases to salaries of the executives are based on our compensation committee’s assessment of the individual’s performance.

When setting the annual base salaries of our executives, our compensation committee primarily considers the scope of an executive’s responsibilities, internal pay equity, the executive’s individual performance, and relative competitiveness with our peer group to ensure that the base salary component of the total direct compensation attracts

and retains superior executive talent. Our compensation committee reviews these criteria collectively but does not assign a weight to any criterion when setting base salaries. Each base salary adjustment is made by our compensation committee subjectively based upon the foregoing.

The base salary rates for each of our named executive officers are set forth in the following table:

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The base salary rates for fiscal 2023 for each named executive officer did not increase from their previous fiscal 2022 year-end levels.

Annual Incentives

Our named executive officers are eligible for annual bonuses based on Company performance, with payment amounts determined by our compensation committee based on the compensation committee’s assessment of performance for the applicable year. The annual incentive plan is intended to focus the entire organization on meeting or exceeding the annual performance goals that are set during the early part of each year and approved by our compensation committee, while also providing significant opportunity to reward individual contributions.

Each named executive officer’s annual bonus opportunity under our annual incentive plan is tied to such executive’s base salary rate in effect at the time of grant. An executive’s annual bonus opportunity generally increases as their ability to affect the Company’s performance increases. Consequently, as an executive’s responsibilities increase, their variable compensation in the form of an annual bonus, which is dependent on Company performance, generally makes up a larger portion of the executive’s total compensation.

The fiscal year 2023 annual bonus opportunity for each of our named executive officers is set forth in the following table:

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Target annual incentive opportunities for each named executive officer were unchanged from their previous fiscal 2022 year-end target levels.

For our fiscal year 2023 annual incentive plan, our compensation committee determined to use the pre-established performance goals noted in the table below. Our compensation committee believes these performance goals reflect commonly recognized measures of financial and operating performance within our industry and are key drivers of sustained value creation for our stockholders. The performance goals and weightings, in addition to our actual performance, are set forth in the following table:

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In April 2023, the compensation committee reviewed our performance against the above-referenced measures, and determined that performance goals were achieved as follows:

Although the achievement of each of the performance goals of fiscal 2023 approached or exceeded the 100% achievement level, the Company’s Board of Directors determined it appropriate to reduce the level of bonus payout against target to 80% based on a number of factors, including macroeconomic market factors and fiscal 2023 strategic cost reduction decisions.

The annual bonuses earned by our named executive officers are based on the base salary earned during fiscal year 2023, the achievement metrics described above, and timing of the Company’s payroll and base salary increases. Based on the foregoing, the annual bonuses earned by our named executive officers for fiscal year 2023 are set forth in the following table:

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As part of our fiscal 2023 bonus program, we granted our named executive officers PSUs tied to our annual performance goals. PSUs granted to our named executive officers as part of the fiscal 2023 annual incentive bonus vested in full in May 2023 in connection with the corporate bonus payout. The grant date fair value of these PSUs is included in the fiscal year 2023 annual bonus amount for each named executive officer in the table above. The number of PSUs granted to each named executive officer and that vested in connection with our fiscal 2023 bonus program were as follows:

Long-Term Incentive Awards

We utilize long-term incentive awards under the 2020 Plan to align executive compensation and performance, incentivize the advancement of our critical business objectives, promote long-term stockholder value creation, and reward and retain key employees. Consistent with this approach, for fiscal 2023, the majority of our named executive officers’ annual compensation was provided in the form of time-based restricted stock units (RSUs) and stock options. As noted above, we plan to increase the use of performance-based equity in the form of PSUs as a percentage of aggregate executive compensation. In fiscal 2024, PSUs are being introduced into the long-term incentive compensation mix and will represent approximately 50% of our named executive officers’ annual long-term incentive grants.

The Compensation Committee believes that equity awards with time-based vesting align the interests of our named executive officers with the interests of our stockholders by promoting the stability and retention of an effective executive team over the longer term. It further believes that by granting our executive officers long-term incentives in the form of equity awards better ensures they take a longer-term view of the business and associated strategies for growth. Meaningful equity ownership afforded by the grant of such long-term equity awards helps attract and retain the named executive officers and other key employees. In consultation with FW Cook, our compensation consultant, the Committee considers the range between the 25th to 75th percentile relative to our peer companies as a reference in determining the target value of equity grants issued upon hire and then annually thereafter. The Committee also factors in the role and experience of the named executive officer, as well as prior compensation level, in determining target value of equity awards. Further, the Committee retains discretion to make adjustments as it deems appropriate to ensure alignment of the interests of named executive officers with those of stockholders or encourage retention.

RSU and stock option awards granted to our named executive officers during fiscal 2023 vest over a three-year period, with 33.3% of the award vesting on the first anniversary of the grant date and the remainder vesting in 24 substantially equal monthly installments thereafter. The vesting of RSUs and stock options is subject to an executive officer’s continued provision of services to us through each applicable vesting date. For grants made to our named executive officers prior to fiscal 2023, vesting for both RSUs and stock options generally occurs over a four-year period, with 25% of the award vesting on the first anniversary of the grant date and the remainder vesting in 36 substantially equal monthly installments thereafter.

In June 2022, based on the Committee’s review of market data from our peer group and factoring in our performance for fiscal year 2022, our compensation committee approved the grant of the following time-based RSUs and options to each of our named executive officers. The vesting period for RSUs and options commenced on June 29, 2022.

Hilton Transition

Michael Hilton was formerly our Chief Innovation Officer prior to becoming a non-employee director in February 2023. In lieu of receiving non-executive director compensation for his Board of Directors service, Mr. Hilton will instead continue to vest in the equity awards he was granted during his time as an employee of the Company until December 31, 2024 and will retain eligibility for his fiscal 2023 annual incentive. Mr. Hilton also will continue to receive health benefits (or equivalent COBRA reimbursement) from the Company until December 31, 2024. Mr. Hilton will not be eligible to receive any non-employee director compensation in any form until after December 31, 2024, at which time he shall be eligible to receive non-employee director compensation consistent with other non-executive directors.

Other Benefits

Employee Benefit and Retirement Programs

We maintain a health and welfare plan and a qualified defined contribution 401(k) plan in which all of our eligible employees, including our named executive officers, may participate. The Company matches 100% of up to the first 3.5% of a participant’s deferral, up to $3,500 per year under the 401(k) plan. Company contributions are vested over a period of four years of service.

Perquisites

We generally do not provide significant perquisites or personal benefits to our named executive officers.

Employment Agreements and Severance Benefits

We provide certain of our named executive officers with certain severance protections in their employment agreements in order to attract and retain an appropriate caliber of talent for such positions. Our employment agreements with the named executive officers and the severance provisions set forth therein are summarized below under “— Compensation Arrangements with our Named Executive Officers” and “— Potential Payments upon Termination or Change in Control.” We intend to periodically review the level of the benefits in these agreements.

Governance and Other Considerations

Clawback Policy

In April 2023, our Board adopted a Clawback Policy that applies to incentive-based compensation received by our executive officers, as each of those terms are defined in 229 C.F.R. Sec. 240.10D-1(d). In the event the Company is required to prepare an accounting restatement due to material noncompliance with any financial reporting measure (also as defined in 229 C.F.R. Sec. 240.10D-1(d)), then the Company will promptly recover any incentive-based compensation received by our executive officers during the three (3) completed fiscal years immediately preceding the date the Company is required to prepare the accounting restatement in excess of the amounts that would have been otherwise received based on the accounting restatement. Such Clawback Policy applies to incentive-based compensation received by an executive officer solely for the period during which they served as an executive officer. The Company’s Compensation Committee shall determine the application and timing of any recoupment of erroneously awarded compensation under the Clawback Policy.

The SEC has adopted final rules implementing the provisions of the Dodd-Frank Wall Street Reform and Consumer Protection Act relating to recoupment of incentive-based compensation, and the Nasdaq stock exchange has proposed listing standards thereunder. We will monitor and amend the Clawback Policy as necessary to reflect the final Nasdaq listing standards during the required timeframe in compliance therewith.

Stock Ownership Guidelines

In April 2023, our Board adopted Stock Ownership Guidelines that require each non-employee director and executive officer to own the Company’s stock at meaningful levels to further align the interests of directors and executives to our stockholders. The Stock Ownership Guidelines set forth three (3) tiers of stock ownership, as follows:

The Stock Ownership Guidelines will be measured annually as of January 1st of each year commencing January 1, 2024. Unvested and unexercised stock options and performance stock units for which the performance-based criteria has not been met do not count towards compliance with the Stock Ownership Guidelines.

Prohibition on Hedging and Pledging

The Company’s Insider Trading Policy (the “Policy”) prohibits directors and employees, including our named executive officers, from (1) engaging in inherently speculative transactions, (2) entering into hedging or monetization transactions involving our Company stock and (3) holding our Company stock in a margin account or pledging our Company stock as collateral for a loan. The Policy also discourages placing standing or limit orders on the Company’s securities. We maintain this Policy because such transactions could create the appearance that the person is trading on inside information, and we believe this Policy serves to further align the interests of our employees, executives and directors with our stockholders’ interests. A summary of the Policy is set forth below:

Inherently Speculative Transactions.   Persons subject to this Policy may not engage in short sales, transactions in put options, call options or other derivative securities on an exchange or in any other organized market, or in any other inherently speculative transactions with respect to the Company’s stock.

Margin Accounts and Pledges.   Persons subject to this Policy may not pledge any Company securities as collateral for a loan and such person may not hold Company securities as collateral in a margin account. Such persons may not have control over these transactions as the securities may be sold at certain times without such person’s consent. A margin or foreclosure sale that occurs when a person subject to this Policy is aware of material, nonpublic information may, under some circumstances, result in unlawful insider trading.

Hedges and Monetization Transactions.   Persons subject to this Policy may not engage in hedging or monetization transactions, through transactions in Company securities or through the use of financial instruments designed for such purpose. Such hedging and monetization transactions may permit a person to own Company securities, but without the full risks and rewards of ownership. When that occurs, the person may no longer have the same objectives as the Company’s stockholders generally.

Tax Implications

One of the factors the Committee considers when determining executive compensation is the anticipated tax treatment to the Company and to the executives of the various payments and benefits. Section 162(m) of the Internal Revenue Code (“Section 162(m)”) generally provides that a publicly held company may not deduct compensation paid to certain covered executive officers to the extent that such compensation exceeds $1,000,000 per executive officer in any year. While our compensation committee generally considers this limit when determining compensation, there are instances in which our compensation committee has concluded, and reserves the discretion to conclude in the future, that it is appropriate to exceed the limitation on deductibility under Section 162(m) to ensure that executive officers are compensated in a manner that it believes to be consistent with the Company’s best interests and those of its stockholders.

COMPENSATION COMMITTEE REPORT

The Compensation Committee of the Board has reviewed and discussed the Compensation Discussion and Analysis required by Item 402(b) of Regulation S-K with management and, based on such review and discussions, the Compensation Committee recommended to the Board that the Compensation Discussion and Analysis be included in this proxy statement and the Company’s Annual Report on Form 10-K for the fiscal year ended February 28, 2023.

THE COMPENSATION COMMITTEE

Jeffrey Brodsky, Chair
Jeffrey Jordan

Patricia Wadors

SUMMARY COMPENSATION TABLE

The following table presents all of the compensation awarded to, earned by, or paid to our named executive officers during the fiscal years ended February 28, 2023, February 28, 2022 and February 28, 2021.

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GRANTS OF PLAN-BASED AWARDS

The following table presents certain information regarding grants of plan-based awards to our named executive officers for the fiscal year ended February 28, 2023. All awards were issued under the 2020 Equity Incentive Plan.

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COMPENSATION ARRANGEMENTS WITH OUR NAMED EXECUTIVE OFFICERS

Rajeev Singh.   In October 2015, we entered into an Employment Agreement with Mr. Singh (the “Singh Employment Agreement”). The Singh Employment Agreement has no specific term, provides for at-will employment and reflects Mr. Singh’s initial annual base salary of $400,000, an initial discretionary target bonus opportunity per year of up to sixty percent (60%) of the base salary, the terms of his initial stock option grant, and severance benefits upon an involuntary termination, as described below in “— Potential Payments upon Termination or Change in Control.”

Stephen Barnes.   On December 1, 2014, we entered into a Letter Agreement with Mr. Barnes (the “Barnes Employment Agreement”). The Barnes Employment Agreement has no specific term, provides for at-will employment and reflects Mr. Barnes’s initial annual base salary of $400,000, a one-time bonus payment of $100,000 paid in April 2015, a discretionary target bonus opportunity per year of up to fifty percent (50%) of the base salary, the terms of his initial stock option grant, and severance benefits upon an involuntary termination, as described below in “— Potential Payments upon Termination or Change in Control.”

Robert Cavanaugh.   On October 26, 2015, we entered into a Letter Agreement with Mr. Cavanaugh (the “Cavanaugh Employment Agreement”). The Cavanaugh Employment Agreement has no specific term, provides for at-will employment and reflects Mr. Cavanaugh’s current annual base salary of $350,000, a discretionary target bonus opportunity per year of up to fifty percent (50%) of the base salary, and the terms of his initial stock option grant. The Cavanaugh Employment Agreement does not contain provisions regarding severance benefits.

Michael Hilton.   On October 26, 2015, we entered into a Letter Agreement with Mr. Hilton (the “Hilton Employment Agreement”). The Hilton Employment Agreement has no specific term, provides for at-will employment and reflects Mr. Hilton’s initial annual base salary of $325,000, a discretionary target bonus opportunity per year of up to fifty percent (50%) of the base salary, and the terms of his initial stock option grant. The Hilton Employment Agreement does not contain provisions regarding severance benefits. The Hilton Employment Agreement was terminated effective February 15, 2023 in connection with Mr. Hilton’s resignation as an executive officer.

 OUTSTANDING EQUITY AWARDS AT FISCAL YEAR-END

The following table presents the outstanding equity incentive plan awards held by each named executive officer as of February 28, 2023.